We report a sequential catalytic asymmetric transfer hydrogenation-carboxylative cyclization for the facile construction of chiral 4-fluoroalkyl 2-oxazolidinones with high enantioselectivity. The resulting 2-oxazolidinones can be easily elaborated to synthetic useful chiral β-fluoroalkyl β-amino alcohols. This research also represents a rare example of catalytic asymmetric sequential reactions using CO2 as a C1 synthon as well as carboxylative cyclization of α-fluoroalkyl propargylamines.